Benzyl Bromide → 1-Benzyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate

HRID 1904455Notes

Reaction equation

HRID 1904455 reaction equation
O1CCC[CH2:2]1.[CH3:6][O:7][C:8](=[O:25])[C@H:9]([CH2:21][CH2:22]SC)[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(Br)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH3:6][O:7][C:8](=[O:25])[C@@H:9]1[CH2:21][CH2:22][CH2:2][N:10]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 11141035Cbz-L-methionine methyl ester

Product 1

HCID 6881681-Benzyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran solution (1 ml) of the compound prepared in Example 7 (146 mg), were successively added dropwise at 0° C. in a nitrogen atmosphere benzyl bromide (0.114 ml, 0.96 mmol) and a tetrahydrofuran solution of tetrabutyl ammonium fluoride (0.48 ml, 0.48 mmol). The mixture was stirred for 1 hour at 0° C., poured into water and extracted with ether. The ether layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The resulting reaction mixture was subjected to column chromatography on silica gel and eluted with a 1:1 mixture of ether and hexane to give the titled compound in an amount of 94 mg (yield, 75% based on the starting materials used in Example 7).

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe resulting reaction mixture
  5. washeluted with a 1:1 mixture of ether and hexane

Sources & evidence

ORD record
ord-fb4619cbdfa0482c9f4d97ce92c290cc
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

Loading…